Hydrazine hydrate (1:1) → HCID 14372560, compound

HRID 1382971Notes

Reaction equation

HRID 1382971 reaction equation
[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[O:7])=[C:4]([O:19][CH2:20][CH2:21][CH2:22][N:23]2C(=O)C3=CC=CC=C3C2=O)[CH:3]=1.O.NN>C(O)C>[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:12][CH3:13])[CH2:14][CH3:15])=[O:7])=[C:4]([O:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 14372559HCID 14372559, compound

Product 1

HCID 14372560HCID 14372560, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-[3-(phthalimide)propoxy]benzamide (4.73 g, 10 mmoles) (prepared in Example 38), 64% hydrazine hydrate (800 mg, 16 mmoles) and absolute ethanol (15 ml) was heated briefly to reflux until clear solution was formed. The solution was heated 16 hours at 55°-57° C. and then 2 hours at reflux. After cooling, a solid was filtered off and washed with ethanol. The combined filtrate and washings were concentrated in vacuo. The residue was dissolved in methylene chloride, and insoluble solid removed by filtration. The filtrate was washed with water, dried and concentrated in vacuo to give a solid product. This was recrystallized from methylene chloride-n-pentane to give 2.96 g (86.3%) of the title compound as white solid, mp 119°-121° C.

Workup

  1. temperaturewas heated briefly
  2. temperatureto reflux until clear solution
  3. customwas formed
  4. temperatureThe solution was heated 16 hours at 55°-57° C.
  5. temperature2 hours at reflux
  6. temperatureAfter cooling
  7. filtrationa solid was filtered off
  8. washwashed with ethanol
  9. concentrationThe combined filtrate and washings were concentrated in vacuo
  10. dissolutionThe residue was dissolved in methylene chloride
  11. custominsoluble solid removed by filtration
  12. washThe filtrate was washed with water
  13. customdried
  14. concentrationconcentrated in vacuo
  15. customto give a solid product
  16. customThis was recrystallized from methylene chloride-n-pentane

Sources & evidence

ORD record
ord-77b4aded5627471585f07d6bfa6a5ef1
Source dataset
uspto-grants-1989_02
Patent number
US04808624

Reaction notes

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